It seemed as though everyone was eager to learn as much as they could about the new couple when photographs of Harry Styles and Olivia Wilde holding hands surfaced online.
Here, we summarize all we currently know about Harry Styles and Olivia Wilde’s romance.
September 2020: Harry Styles will star in Olivia Wilde’s upcoming film
Styles has taken Shia LaBeouf’s position in the upcoming film Don’t Worry, Darling, according to a report from Deadline. The project is directed by Wilde, and Katie Silberman wrote the screenplay, which was adapted from the Van Dyke brothers’ original script. Chris Pine, Florence Pugh, and Wilde all play supporting roles in the film.
November 2020: After Harry was cast, Olivia talks about doing a “victory dance.”
Wilde discusses her feelings over the former member of One Direction being cast in Don’t Worry Darling in an interview for Styles’ Vogue cover story. Wilde also talks about the joy she and the movie’s costume designer, Arianne Phillips, who is also an Oscar candidate, share.
“She and I did a little victory dance when we heard that we officially had Harry in the film, because we knew that he has a real appreciation for fashion and style,” Wilde explained (via People). “And this movie is incredibly stylistic. It’s very heightened and opulent, and I’m really grateful that he is so enthusiastic about that element of the process—some actors just don’t care.”
“To me, he’s very modern, and I hope that this brand of confidence as a male that Harry has—truly devoid of any traces of toxic masculinity—is indicative of his generation and therefore the future of the world,” Wilde said. “I think he is in many ways championing that, spearheading that. It’s pretty powerful and kind of extraordinary to see someone in his position redefining what it can mean to be a man with confidence.”
In November 2020, Olivia and Jason Sudeikis announce their separation.
Olivia Wilde and Jason Sudeikis announced their separation in mid-November. People described the split as “amicable” and praised the former couple for their commitment to their two children, Otis Alexander, 6, and Daisy Josephine, 4.
A source told People, “The split happened at the beginning of the year… It’s been amicable and they’ve transitioned into a great co-parenting routine. The children are the priority and the heart of the family’s relationship.” Entertainment Tonight appeared to confirm this narrative, with a source allegedly close to Wilde calling the split “mutual.”
“They just fell out of love in a romantic way, but still have love towards one another as people,” the source explained to ET. “They consider themselves friends and co-parents first and foremost.” Another source added, “there was absolutely no drama or scandal, they just didn’t work as a couple anymore. If you’re looking for a juicy story, there just isn’t one.”
The initial romantic rumors about Wilde and Sudeikis surfaced in November 2011, and a little over a year later, Sudeikis proposed to Wilde.
Olivia and Harry hold hands while attending a wedding in January 2021.
Early in 2021, images of Wilde and Styles holding hands appear online, sparking a flood of enquiries. The new couple were sighted at the San Ysidro Ranch in Montecito, California, where his agent was being married.
The new pair have been dating for some time, an insider told People. A source told Entertainment Tonight that Wilde and Styles met while filming Don’t Worry, Darling, and that their romance developed from there.
“Olivia and Harry are together for long days on set and have gotten to know each other really well, so it’s all very organic,” the source revealed. “[Olivia] wouldn’t let a romantic relationship get in the way of a professional one, so anything they’re doing is being done thoughtfully.”
More PDA seems to confirm their position as the newest power couple in Hollywood. Additionally, a source tells Us Weekly that Wilde and Styles made a conscious effort to conceal their relationship during filming.
“Olivia and Harry were able to keep their relationship under wraps for a bit before it became public knowledge,” Us Weekly’s source revealed. “They were very careful about it and even sleuthy at times, although the small group of people who were on set with them every day eventually figured it out.”
In January 2021, Jason is the subject of contradictory reports.
What Sudeikis, Wilde’s ex, thinks of Styles’ new relationship with her is currently unknown. According to a person who spoke with ET, Wilde and Sudeikis split up “almost a year ago … it’s not like she’s rushing into something.” The source continued, “Olivia and Jason talk all the time and are still close because of the kids. It’s highly unlikely he was blind-sided by this news.” The insider who spoke to Us Weekly agrees, “Harry did not break up an engagement,” stating that when Wilde first met Styles, her relationship with Sudeikis was “already done.”
But an insider offered an entirely different tale to People, saying, “[Jason Sudeikis] is absolutely heartbroken about the split. There is still a lot of love there, and he would like to have hope that maybe there’s a way for them to repair things. But what happens next remains to be seen.”
February 2021: Olivia and Harry are “very happy” together.
According to unnamed sources, Styles and Wilde are still going strong. People was informed by a source that Styles and Wilde “seem very serious” and “spend all their time together.” According to the source, “[Olivia] is also very happy with Harry.”
According to a source who spoke to People about the status of Don’t Worry Darling’s production, “Olivia and Harry continue to film in L.A. Filming has been tricky because of COVID. They have shut down the set several times for testing and breaks … Olivia is amazing to work with though. She stays calm and very focused despite all the breaks.”
February 2021: As Don’t Worry Darling filming comes to an end, Olivia praises Harry on Instagram.
In an Instagram post about Styles, director Wilde chose to show the world how much she admires him. “Little known fact: most male actors don’t want to play supporting roles in female-led films. The industry has raised them to believe it lessens their power (i.e financial value) to accept these roles, which is one of the reasons it’s so hard to get financing for movies focusing on female stories. No joke, it is harrrrrd to find actors who recognize why it might be worth it to allow for a woman to hold the spotlight,” Wilde wrote. “Enter: @harrystyles, our ‘Jack’ . Not only did he relish the opportunity to allow for the brilliant @florencepugh to hold center stage as our ‘Alice’, but he infused every scene with a nuanced sense of humanity. He didn’t have to join our circus, but he jumped on board with humility and grace, and blew us away every day with his talent, warmth, and ability to drive backwards. 👊 #dontworrydarling.”
Along with the rest of the cast, the pair posed for a picture as filming came to an end.
Olivia and Jason rekindle their friendship in February 2021 as Olivia’s romance with Harry deepens.
While Wilde is “so happy” in her current relationship with the former member of One Direction, a source for Entertainment Tonight claimed that she and Sudeikis are now “in a good place, too.”
“Jason was initially really hurt about Harry and Olivia’s relationship, but now that he’s doing his own thing, things between him and Olivia have gotten better,” said the insider. “They’re rebuilding their friendship again and co-parenting together.”
After Harry’s first Grammy win in March 2021, Olivia sweetly supports him on Instagram.
Styles received his first Grammy at the 63rd annual Grammy Awards ceremony for his top-charting song, “Watermelon Sugar,” which was nominated for Best Pop Solo Performance. Through her Instagram Stories, where she posted images of other music greats, Wilde seemed to subtly support him.
Wilde referred to a Mick Jagger performance in which the singer appeared onstage in just a leather jacket and a scarf (in case that sounds familiar). Additionally, she shared a photo of Paul McCartney munching on a piece of watermelon, which followers perceived as a clear reference to Styles’ Grammy-winning song.
In April 2021, Harry and Olivia spend a lot of “alone time” in the UK.
The couple is spending time together across the border, according to a source who spoke to Entertainment Tonight. “Filming during a pandemic in L.A. was pretty all-consuming,” the insider said of Wilde and Styles working together on Don’t Worry Darling. “Now they’re able to unwind, relax, and really enjoy some one-on-one time.”
The two have continued to maintain a low profile in the UK. “Their idea of a good time is going for a long walk and ducking into a neighborhood pub,” said the source.
In the meantime, the dynamics of Wilde and Jason Sudeikis’ co-parenting have also improved. “All [Olivia’s] ever wanted is for them to have a united front,” another insider previously told the outlet. “They are and always will be a family.” The couple, who dated for almost ten years and were engaged, have two kids together: Daisy Sudeikis, four, and Otis, seven. The second insider continued, “She is very supportive of Jason and is pleased of him.”
In June 2021, a source claims that Harry and Olivia have “grown even closer as a couple.”
According to a source who spoke with ET Online, Styles and Wilde have “grown even closer as a couple” while staying together in London, where they have “been going on walks outside in the park and not hiding their relationship.”
“Yesterday, they enjoyed lunch outside and looked incredibly cute together,” the source added. “They were both in a great mood and left the restaurant holding hands. Harry put his arm around Olivia as they walked back to her house.”
Harry and Olivia kiss aboard a yacht in Italy in July 2021.
Styles and Wilde were spotted engaging in some intense boat PDA while hanging out in Italy. In the pictures, they are seen cuddling, kissing, and resting in the sun together while wearing matching royal blue swimsuits
In September 2021, Olivia supports Harry at the start of his stadium tour.
At the Love on Tour concert’s opening night on Saturday in Las Vegas, Wilde was seen standing by Styles’ side. Her entrance from the backstage area to her seats was captured on Twitter, and a different eyewitness told E! News that Wilde sang along to the majority of his songs. The witness reports, “She was so happy and dancing all night.”
“It was very cute. She was singing along to almost every song…and having a good time with the people she was with,” they claimed.
Olivia is seen in November 2021 with what looks to be Harry’s gold cross necklace.
The duo appears to be raiding each other’s wardrobes. Wilde was seen sporting a gold cross necklace that is strikingly similar to one of Styles’ necklaces while attending the Gucci Love Parade fashion show. According to People, a sharp-eyed admirer even created a TikTok noting the connection.
Olivia is “happier than she’s ever been” in December 2021.
Wilde quietly addressed the media attention surrounding the relationship’s 10-year age difference in a new interview. She doesn’t mention Styles by name, but she makes it seem like they are in love and content with their relationship. “It’s obviously really tempting to correct a false narrative,” she told Vogue. “But I think what you realize is that when you’re really happy, it doesn’t matter what strangers think about you. All that matters to you is what’s real, and what you love, and who you love.”
She continued by saying that social media had made it more challenging for even the typical person to avoid constant observation. “In the past 10 years, as a society, we have placed so much more value on the opinion of strangers rather than the people closest to us,” she said. “I’m happier than I’ve ever been. And I’m healthier than I’ve ever been, and it’s just wonderful to feel that.”
Harry is getting to know Olivia’s children as of December 2021.
As the two people get near to their one-year anniversary, Wilde has advanced their romance by introducing Styles to her two kids, Otis, 7, and Daisy, 5, whom she had with her ex-husband Jason Sudeikis.
According to an insider, “Harry is slowly getting to know her kids. Olivia is also spending time with Harry’s mom,” adding that the couple “have a great relationship.”
Despite their hectic schedules—Styles finishing off his Love on Tour and Wilde filming the historical drama Babylon—the couple has been able to strengthen their bond.
“[They try] to see each other as much as possible,” the insider continued. “Olivia has been flying nonstop between L.A., where her kids live, to join Harry on tour.”
The insider said, Wilde has frequently been spotted out and about sporting merchandise from her boyfriend’s concert tour. Adding “She always seems focused on just making it all work. She is really Harry’s biggest fan.”
Harry and Olivia celebrate his birthday in London in February 2022.
This year, Wilde gave fans a glimpse into the couple’s birthday celebrations. The day after Styles turned 28, on February 2, she uploaded two pictures of herself on her Instagram Stories decked out in a jumpsuit by Kwaidan Editions, according to People.
The second image, which had the caption “Happy happy,” showed her standing behind a table lighted by candles while the first was a mirror selfie.
Later that week, the two were seen in public in London at the “Francis Bacon: Man and Beast” exhibition at the Royal Academy of Arts. The celebrities maintain a low profile as they look at the art in the pictures, which you can see here. “Francis Bacon at the Royal Academy if you’re in London go, go, go!”, said Wilde beside a photo of one of the works she posted to her Story.
Harry discusses working with Olivia as a director on Don’t Worry, Darling in May 2022.
Styles appeared on Howard Stern’s SiriusXM program, when Stern reportedly asked him, “You fell in love on a movie set?”
Harry Replied “Oh, wow, how to answer this question?” “I had a wonderful experience being directed by Olivia. I think there is something that obviously … acting is very uncomfortable at times. I think you have to trust a lot.”
“Being able to trust your director is a gift,” he continued. Adding “That was very helpful, and it really meant for a really nice experience working on that movie.”
Olivia promotes Harry’s new album on Instagram in May 2022.
On the day it was released, Wilde made a nice homage to Styles’ album Harry’s House. She uploaded his song “Music for a Sushi Restaurant,” using it as the background music for a black-and-white scene from the 2018 movie Cold War in which the female protagonist dances around a bar while sipping a cocktail. According to Page Six, she also included an emoji showing hands lifted in adoration in the post’s description.
The song’s lyrics appear to make reference to Wilde’s emerald eyes, which might be a nod to the actress. “Green eyes, fried rice, I could cook an egg on you / Late night, game time, coffee on the stove, yeah,” Styles sings.
Harry and Olivia are sighted in NYC in August 2022 while enjoying a rare date night.
The pair was spotted spending a special day together, beginning with a workout when they were seen kissing, followed by a date at the popular SoHo restaurant Rubirosa. Wilde wore a navy T-shirt and a long, white-and-blue toile de Jouy skirt for the date, while Styles wore a summer sweater with an open flower-shaped knit and brown pinstriped pants.
August 2022: Harry explains why he keeps his romances private as Olivia praises his performance in Don’t Worry, Darling.
Wilde lauded her boyfriend’s performance in the psychological thriller in a new interview with Rolling Stone. Specifically referring to a “dark as hell … strange scene, full of fascist references, and a disturbing amount of male rage,” in which Styles costarred with Chris Pine, Wilde said, “Harry took it to another level. He was so fully in the moment, he began screaming the lines to the crowd, in this primal roar, that was way more intense than anything we expected from the scene.”
His work “left us all in tears,” she said.
“The camera operator followed [Harry] as he paced around the stage like a kind of wild animal,” Wilde continued. “We were all gobsmacked at the monitor. I think even Harry was surprised by it. Those are the best moments for an actor—when you’re completely outside your body.”
Styles was open and honest about his decision to keep his sexuality and love relationships private during the conversation.
“I’ve never talked about my life away from work publicly and found that it’s benefited me positively,” he told the magazine. “There’s always going to be a version of a narrative, and I think I just decided I wasn’t going to spend the time trying to correct it or redirect it in some way.”
He added, “Sometimes people say, ‘You’ve only publicly been with women,’ and I don’t think I’ve publicly been with anyone. If someone takes a picture of you with someone, it doesn’t mean you’re choosing to have a public relationship or something.”
Styles made the following comment on his upcoming role in My Policeman as a closet gay police officer: “I think everyone, including myself, has your own journey with figuring out sexuality and getting more comfortable with it.”
In August 2022, Olivia opens up on the need of protecting their privacy.
The director talked candidly about her and Styles’ choice to keep private issues of the heart out of the public eye in an interview with Variety. “I’m not going to say anything about it because I’ve never seen a relationship benefit from being dragged into the public arena,” she said. “We both go out of our way to protect our relationship; I think it’s out of experience, but also just out of deep love.”
According to Wilde, the public and tabloids shouldn’t view her breakup with Jason Sudeikis and the ensuing disruption of their family’s relationship as a spectacle. “The last two years, my family has gone through this kind of restructuring and a revolution that should be a totally personal experience,” she said. “And it’s not. The most painful element of it has been women shaming me for making a decision that was for my own health and happiness.”
She continued by saying that people’s assessments of her based only on paparazzi photos of her with Styles have misogynistic undertones. “When people see me not with my kids, it’s always ‘How dare she,'” Wilde said. “I’ve never seen anyone say that about a guy. And if he is with his kid, he’s a fucking hero.”
Styles, however, lauded Wilde for her dedication while filming Don’t Worry, Darling. “As a director, Olivia is incredibly focused. She communicated what she was looking for from the cast with both clarity and respect,” he told the outlet of his girlfriend. “I think transitioning from acting into directing has made her a director who knows how to get the best out of everyone.”
On September 5, 2022, Olivia and Harry walk the red carpet for the Don’t Worry Darling global premiere.
Along with the cast members Florence Pugh, Gemma Chan, Sydney Chandler, and Chris Pine, the pair attended the Don’t Worry Darling world premiere at the 79th Venice International Film Festival. Prior to the screening, they also went to a press conference.
They seemed to separate themselves during group shots to keep the focus on the movie rather than their connection throughout the festivities.
Olivia refutes allegations that she left her ex Jason Sudeikis for Harry on September 8, 2022.
In a new interview with Vanity Fair, Wilde was open and honest about the rumors that she was seeing Styles before her romance with Sudeikis ended.
“The complete horseshit idea that I left Jason for Harry is completely inaccurate,” she said. “Our relationship was over long before I met Harry. Like any relationship that ends, it doesn’t end overnight. Unfortunately, Jason and I had a very bumpy road, and we officially dissolved the relationship towards the beginning of the pandemic. We were raising two kids during lockdown, so we co-parented through that time. Once it became clear that cohabitating was no longer beneficial for the children, it became the responsible thing to not, because we could be better parents as friends who live in different houses.”
She also bemoaned the constant criticism she gets from females who presume she neglects her children whenever paparazzi snap pictures of her and Styles.
“I’ve had women judging me for separating from Jason. There are people who feel entitled to hurl horrendous insults at me and my family. Telling me I’m a terrible mother. Threatening me and my kids or saying I should lose my children,” she said, adding that Sudeikis shares equal custody of their children. “When they are with their father, I trust him to be a great parent. So when they’re not with me, I continue to live my life. But the judgment I’ve seen from people for living my life … I was like, ‘Why are these women finding pleasure in this moment? Is it because it somehow makes them feel better about their lives, judgments, and choices without ever wondering why I might have made those choices?'”
Wilde applauded her boyfriend’s willingness to take chances on the Don’t Worry, Darling set in the interview as well.
“My thing with Harry was that I knew he was fearless,” she said. “I’d rather work with a non-actor who’s fearless than a trained actor who is full of hang-ups and baggage and judgment. What I love about working with singers and dancers is they commit 100 percent because, as a dancer, if you don’t commit 100 percent, you get hurt. With singers, it’s the same. If they sing at 30 percent, that song doesn’t work. I think actors sometimes think they can get away with 30 percent.”
On September 19, 2022, Olivia and Harry attend the after-party for the Don’t Worry Darling NYC premiere.
For the Don’t Worry Darling world premiere in New York City, the pair presented themselves in an elegant manner. Styles donned a full Gucci outfit for the opulent event, which included a velvet double-breasted jacket, a sky blue oxford shirt, navy slacks with ivory striped patterns, and a pair of black leather boots with buckle accents. In contrast, Wilde radiated classic style in a sleek, long-sleeved black gown.
The two were seen together leaving the premiere for the after-party.
September 2022: Olivia posts a photo of Harry on Instagram to mark the release of Don’t Worry Darling.
A photo of Wilde, Styles, Florence Pugh, and screenwriter Katie Silberman seated at a table on the Don’t Worry Darling set was posted by Wilde in celebration of the movie’s premiere.
“Don’t Worry Darling is officially open. Aaahhhhhhhh!!!!!!!” the caption read. “I’m so deeply grateful for this experience, and for the extraordinary effort of the group of artists who made it happen. We got together to tell a story for you, and we hope you have fun with it.
On September 21, 2022, Olivia attends Harry’s concert in New York City.
On September 21, the actress and director wore a chic white cut-out Stella McCartney dress to her boyfriend’s concert at Madison Square Garden in New York. She accessorized the ensemble with black sunglasses, a white feather boa, gold jewelry by Anita Ko, and a pair of clunky Casadei black platform boots. Wilde was spotted dancing in the arena as the “As It Was” singer enthralled the audience.
October 24, 2022: Olivia wears Harry’s merch while out in L.A.
While leaving for a workout in Los Angeles, Wilde was spotted sporting her boyfriend’s tour merchandise. The outfit includes gray sweatshirt with the words “Harry’s House,” the title of the singer’s most recent album and current tour, black leggings, matching sneakers, and other black accessories.
In addition to dancing to his music backstage, the actress and producer is frequently spotted cheering Styles on during his performances.
November 15, 2022: Olivia brings her kids to Harry’s concert.
Wilde made sure to attend one of Styles’ performances in Los Angeles and she even brought along a few special friends. Fans posted footage of the filmmaker dancing to the song with her ex-husband Jason Sudeikis’ children, Otis, 8, and Daisy, 6, who she shares.
Styles just received Grammy nominations for Album of the Year, Song of the Year, Record of the Year, and Music Video of the Year. Their appearance coincides with this.
November 18th 2022: Harry Styles and Olivia Wilde Reportedly Are ‘Taking a Break’ After Almost 2 Years of Dating.
Olivia Wilde and Harry Styles’ relationship is now on hold. According to several sources (People), the almost two-year-old pair is “taking a break” from dating. Put it down to distance and scheduling, a source said.
“He’s still touring and is now going abroad. She is focusing on her kids [Otis and Daisy, with ex Jason Sudeikis] and her work in L.A.,” the source said. “It’s a very amicable decision.”
“They’re still very close friends,” the source added.
The site was also informed by a pal that Wilde and Styles aren’t focusing on the same things right now.
“Right now, they have different priorities that are keeping them apart,” the friend said.
They remain “very close friends” after separating as of February 23, 2023.
Several months after their breakup, Wilde and Styles are still friendly and have been focusing on their respective objectives.
“They’re still very close friends,” an insider tells People, adding that Wilde has been preoccupied with co-parenting alongside ex-fiancé Jason Sudeikis and embarking on new directorial projects. “There’s no animosity whatsoever. Plus, she’s got many different directing projects in the works.”
“Right now, they have different priorities that are keeping them apart,” a different pal informs the outlet.
